Typically, adolescence is a time when individuals begin to make consequential, life-framing decisions. However, much of the decision-making literature focuses on high-risk decisions, such as the use of drugs and alcohol, while much less is known about how adolescents make positive decisions, for example, regarding their educational or career goals. Moreover, much of the literature describes a “typical” adolescent, and less is known about atypical youth, particularly those at-risk for delinquency. This article explores these understudied topics. It first provides a model of decision making which includes the decision-maker’s goals, explores how goal setting impacts the decision-making process, and reviews what is known about decision making among at-risk youth. Then it discusses the ChallenNGe Academy, a voluntary, residential National Guard-sponsored program which works with habitual high school truants to positively change their lives.